Crazy problem

hey i have jailbroken 1.1.4 about 27 times.
but every time i do it shows the loading spiny thingy and stays like that untill i do a manual reboot than it usually gos to recovery mode after doing it 27 times i think it could be one of these reasons causing it
1. bad jailbreak method i used the softupgrade because its the only one that works if you have a mac with 16 gb ipod
2. i used bosstool and after installer says error something directory wrong idk if its bosstool doing this but it seems using it triggers it to happen.
3. the themes fix with that fixes the not being able to see the theme after you download it seem to make it mess up.
4. the main trick that makes summerboard work messes it up mabey im not sure yet though.
5. reinstaling installer always results in the spinny thing idk why but if your asking why i reinstalled it its because a lot of time it fixes the error wrong directory thing.

okay so if you have a substitute or any way of helping me such as a different jailbreak for mac or another way of fixing having no room after softupgrade please post a reply thanx